Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation

Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation

Del Moro, F.; Crotti, P.; Di Bussolo, V.; Macchia, F.; Pineschi, M.

Organic Letters 5(11): 1971-1974

2003

[reaction: see text] The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the pi-orbital of the double bond and the sigma-bond connecting the leaving group ever observed for an S(N)2'-cuprate alkylation.